(2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid

Base Information

Chemical Name:(2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid
CAS No.:654666-12-3
Molecular Formula:C₂₉H₃₈N₄O₇S
Molecular Weight:586.709
Hs Code.:

Synonyms:(2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid

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Chemical Property of (2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid

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Technology Process of (2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid

There total 11 articles about (2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 154445-78-0
2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonyl chloride

: 1026656-91-6
(2S,4R)-4-(2-Guanidino-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

: 654666-12-3
(2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1021/jm030232j

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 654666-12-3
(2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1: aq. NaOH / 20 h / 20 °C

2: 6.0 g / 6 h / 80 °C

3: 84 percent / PDC; MS 4A / CH₂Cl₂ / 2 h / 20 °C

4: 98 percent / LiAlH(OtBu)3 / tetrahydrofuran / 2 h / -78 °C

5: cyanomethylenetributylphosphorane / toluene / 20 h / 100 °C

6: Mg; HgCl₂ / methanol; tetrahydrofuran / 2 h / 20 °C

7: CoCl₂*H₂O; NaBH₄ / methanol / 2 h / -20 °C

8: tetrahydrofuran / 12 h / 20 °C

9: TFA / CH₂Cl₂ / 10 h / 0 °C

10: aq. NaOH / tetrahydrofuran / 12 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; magnesium; lithium tri-t-butoxyaluminum hydride; cyanomethylenetributyl-phosphorane; trifluoroacetic acid; cobalt(II) chloride; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; toluene; 5: Mitsunobu type reaction;
DOI:10.1021/jm030232j

Reference yield:

: 72289-52-2
(2S,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester

: 654666-12-3
(2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / PDC; MS 4A / CH₂Cl₂ / 2 h / 20 °C

2: 98 percent / LiAlH(OtBu)3 / tetrahydrofuran / 2 h / -78 °C

3: cyanomethylenetributylphosphorane / toluene / 20 h / 100 °C

4: Mg; HgCl₂ / methanol; tetrahydrofuran / 2 h / 20 °C

5: CoCl₂*H₂O; NaBH₄ / methanol / 2 h / -20 °C

6: tetrahydrofuran / 12 h / 20 °C

7: TFA / CH₂Cl₂ / 10 h / 0 °C

8: aq. NaOH / tetrahydrofuran / 12 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; magnesium; lithium tri-t-butoxyaluminum hydride; cyanomethylenetributyl-phosphorane; trifluoroacetic acid; cobalt(II) chloride; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; toluene; 3: Mitsunobu type reaction;
DOI:10.1021/jm030232j